WO2017062523A2 - Oil compositions and methods of making - Google Patents
Oil compositions and methods of making Download PDFInfo
- Publication number
- WO2017062523A2 WO2017062523A2 PCT/US2016/055599 US2016055599W WO2017062523A2 WO 2017062523 A2 WO2017062523 A2 WO 2017062523A2 US 2016055599 W US2016055599 W US 2016055599W WO 2017062523 A2 WO2017062523 A2 WO 2017062523A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- weight
- ester fraction
- fatty acids
- epa
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title abstract description 31
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 35
- 230000000813 microbial effect Effects 0.000 claims abstract description 12
- 239000003921 oil Substances 0.000 claims description 247
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 189
- 150000002148 esters Chemical class 0.000 claims description 168
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 121
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 121
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 121
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 121
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 121
- 239000000194 fatty acid Substances 0.000 claims description 121
- 229930195729 fatty acid Natural products 0.000 claims description 121
- 150000004665 fatty acids Chemical class 0.000 claims description 115
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 107
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 93
- 238000000526 short-path distillation Methods 0.000 claims description 57
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 claims description 42
- 244000005700 microbiome Species 0.000 claims description 30
- 235000013305 food Nutrition 0.000 claims description 23
- 238000004821 distillation Methods 0.000 claims description 22
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 21
- 238000004508 fractional distillation Methods 0.000 claims description 18
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 18
- 229940012843 omega-3 fatty acid Drugs 0.000 claims description 15
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 claims description 14
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 claims description 14
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 14
- 239000010408 film Substances 0.000 claims description 11
- 239000006014 omega-3 oil Substances 0.000 claims description 11
- 241000598397 Schizochytrium sp. Species 0.000 claims description 10
- 235000021342 arachidonic acid Nutrition 0.000 claims description 10
- 229940114079 arachidonic acid Drugs 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 8
- 241000235575 Mortierella Species 0.000 claims description 6
- 239000011552 falling film Substances 0.000 claims description 6
- 241000894007 species Species 0.000 claims description 6
- 241000907999 Mortierella alpina Species 0.000 claims description 5
- 241000233675 Thraustochytrium Species 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 4
- 235000013336 milk Nutrition 0.000 claims description 4
- 210000004080 milk Anatomy 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 235000013350 formula milk Nutrition 0.000 claims description 3
- 239000008267 milk Substances 0.000 claims description 3
- 235000016709 nutrition Nutrition 0.000 claims description 3
- 235000020665 omega-6 fatty acid Nutrition 0.000 claims description 3
- 229940033080 omega-6 fatty acid Drugs 0.000 claims description 3
- 235000013361 beverage Nutrition 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 235000003869 genetically modified organism Nutrition 0.000 claims 2
- 239000002537 cosmetic Substances 0.000 claims 1
- 235000015872 dietary supplement Nutrition 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 172
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 60
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000523 sample Substances 0.000 description 32
- 125000004494 ethyl ester group Chemical group 0.000 description 31
- 241001465754 Metazoa Species 0.000 description 28
- 125000004185 ester group Chemical group 0.000 description 19
- 238000012856 packing Methods 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 17
- -1 fatty acid ester Chemical class 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 235000021323 fish oil Nutrition 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 238000005809 transesterification reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 8
- 239000010779 crude oil Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 6
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 description 6
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- 235000019688 fish Nutrition 0.000 description 6
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000199912 Crypthecodinium cohnii Species 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 4
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 4
- 229960002733 gamolenic acid Drugs 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000283086 Equidae Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001467333 Thraustochytriaceae Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000020667 long-chain omega-3 fatty acid Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000199913 Crypthecodinium Species 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- 241000199914 Dinophyceae Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000235395 Mucor Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 241001125048 Sardina Species 0.000 description 2
- 241000233671 Schizochytrium Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 241001491678 Ulkenia Species 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940013317 fish oils Drugs 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- SOQKXJABGLKWQX-UHFFFAOYSA-N octacosaoctaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCCC(O)=O SOQKXJABGLKWQX-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 210000001525 retina Anatomy 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000238426 Anostraca Species 0.000 description 1
- 241000238582 Artemia Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001138693 Botryochytrium Species 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- 241000282421 Canidae Species 0.000 description 1
- 241000282668 Cebus Species 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000282551 Cercopithecus Species 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 241000195628 Chlorophyta Species 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 241000206751 Chrysophyceae Species 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 241001454694 Clupeiformes Species 0.000 description 1
- 241001480517 Conidiobolus Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000723298 Dicentrarchus labrax Species 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241001480508 Entomophthora Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000282818 Giraffidae Species 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000282596 Hylobatidae Species 0.000 description 1
- 241001125831 Istiophoridae Species 0.000 description 1
- 241001219832 Lobosporangium Species 0.000 description 1
- 241001417902 Mallotus villosus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 241001306135 Oblongichytrium Species 0.000 description 1
- 241000238413 Octopus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000282579 Pan Species 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 241000282520 Papio Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000269980 Pleuronectidae Species 0.000 description 1
- 241001098054 Pollachius pollachius Species 0.000 description 1
- 241000282405 Pongo abelii Species 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 241000197220 Pythium insidiosum Species 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000700141 Rotifera Species 0.000 description 1
- 241000277331 Salmonidae Species 0.000 description 1
- 241000233667 Saprolegnia Species 0.000 description 1
- 241000269851 Sarda sarda Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 241000238371 Sepiidae Species 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241001223864 Sphyraena barracuda Species 0.000 description 1
- 241001466451 Stramenopiles Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000276707 Tilapia Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000019513 anchovy Nutrition 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000008131 children development Effects 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 230000008175 fetal development Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 229940106134 krill oil Drugs 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- WBIUOUBFNXEKBA-UHFFFAOYSA-N lithium;2-methylpropan-1-olate Chemical compound [Li]OCC(C)C WBIUOUBFNXEKBA-UHFFFAOYSA-N 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- XMAFBJJKWTWLJP-UHFFFAOYSA-N lithium;butan-2-olate Chemical compound [Li+].CCC(C)[O-] XMAFBJJKWTWLJP-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
- HAUKUGBTJXWQMF-UHFFFAOYSA-N lithium;propan-2-olate Chemical compound [Li+].CC(C)[O-] HAUKUGBTJXWQMF-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 235000010598 long-chain omega-6 fatty acid Nutrition 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 1
- ZUPDNLCLXSWMAE-UHFFFAOYSA-N potassium;butan-2-olate Chemical compound [K+].CCC(C)[O-] ZUPDNLCLXSWMAE-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001448 refractive index detection Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- VSCLJRSWEGZJNY-UHFFFAOYSA-N sodium;butan-2-olate Chemical compound [Na+].CCC(C)[O-] VSCLJRSWEGZJNY-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- oil compositions that are enriched in polyunsaturated fatty acids; compositions containing the oil compositions; and methods of making and using the oil compositions.
- the oil is preferably a microbial or marine oil.
- Fatty acids are classified based on the length and saturation characteristics of the carbon chain. Fatty acids are termed short chain, medium chain, or long chain fatty acids based on the number of carbons present in the chain, are termed saturated fatty acids when no double or triple bonds are present between the carbon atoms, and are termed unsaturated fatty acids when double or triple bonds are present. Unsaturated long chain fatty acids are monounsaturated when only one double or triple bond is present and are polyunsaturated when more than one double or triple bond is present.
- PUFAs Polyunsaturated fatty acids
- omega-3 (n-3) fatty acids contain a first double bond at the third carbon counting from the methyl terminal
- omega-6 (n-6) fatty acids contain a first double bond at the sixth carbon.
- DHA docosahexaenoic acid
- LC-PUFA omega-3 long chain polyunsaturated fatty acid
- omega-3 LC-PUFAs include eicosapentaenoic acid (“EPA”), designated as “20:5 n-3,” and omega-3 docosapentaenoic acid (“DPA n-3”), designated as “22:5 n-3.
- Omega-6 LC-PUFAs include arachidonic acid (“ARA”), designated as “20:4 n-6,” and omega-6 docosapentaenoic acid (“DPA n-6”), designated as "22:5 n-6.”
- Omega-3 fatty acids are biologically important molecules that affect cellular physiology due to their presence in cell membranes, regulate production and gene expression of biologically active compounds, and serve as biosynthetic substrates.
- DHA for example, accounts for approximately 15%-20% of the fatty acids making lipids in the human cerebral cortex, 30%-60% of the fatty acids making lipids in the retina, is concentrated in the testes and sperm, and is an important component of breast milk. Berge, J. P., and Barnathan, G.. Adv. Biochem. Eng. Biotechnol. 96:49-125 (2005).
- DHA accounts for up to 97% of the omega-3 fatty acids in the brain and up to 93% of the omega-3 fatty acids in the retina. Moreover, DHA is essential for both fetal and infant development as well as maintenance of cognitive functions in adults. Id. Because omega-3 fatty acids are not synthesized de novo in the human body, these fatty acids must be derived from nutritional sources. However, sources of omega-3 fatty acids can vary in the identity and amounts of LC-PUFAs produced. As such, a continuing need exists for omega-3 fatty acid sources having high amounts of LC-PUFAs with desirable LC-PUFA profiles and for oils that contain higher concentrations of LC-PUFAs.
- Previous concentration methods have been shown to require numerous steps to achieve a desired concentration level, resulting in an inefficient process while often not obtaining the desired LC-PUFA content or profile. Other known methods are costly and time-consuming. Further, previous concentration methods have not provided a method of separation and concentration in one continuous process that provides a desired LC-PUFA content and profile. The inventors have surprisingly found a method of separation and concentration of oils comprising polyunsaturated fatty acids to produce desirable LC-PUFA profiles having higher concentrations of LC-PUFAs that is less costly and time-consuming than previous methods.
- the present invention is directed to an oil comprising an ester fraction, wherein at least about 70% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and from about 0.5% to about 5% by weight of the fatty acids in the ester fraction is docosapentaenoic acid n-3 (DPA n-3). In some embodiments, less than about 5% by weight of the fatty acids in the ester fraction is eicosapentaenoic acid (EPA). In some embodiments, from about 0.1% to about 5% by weight of the fatty acids in the ester fraction is EPA.
- DHA docosahexaenoic acid
- DPA n-3 docosapentaenoic acid n-3
- EPA eicosapentaenoic acid
- from about 0.1% to about 5% by weight of the fatty acids in the ester fraction is EPA.
- the ester fraction comprises at least about 70% by weight of the oil.
- the present invention is directed to an oil comprising an ester fraction, wherein at least about 70% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and from about 3% to about 13% by weight of the fatty acids in the ester fraction is docosapentaenoic acid n-3 (DPA n-3) and docosapentaenoic acid n-6 (DPA n-6).
- DHA docosahexaenoic acid
- DPA n-6 docosapentaenoic acid n-6
- from about 1 % to about 5% by weight of the fatty acids in the ester fraction is DPA n-3. In some embodiments, from about 2% to about 8% by weight of the fatty acids in the ester fraction is DPA n-6. In some embodiments, less than about 5% by weight of the fatty acids in the ester fraction is eicosapentaenoic acid (EPA). In some embodiments, from about 0.1 % to about 5% by weight of the fatty acids in the ester fraction is EPA. In some embodiments, the ester fraction comprises at least about 70% by weight of the oil.
- the present invention is also directed to an oil comprising an ester fraction, wherein at least about 70% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and the amount of DHA in the ester fraction is at least about 65% by weight of the total omega-3 fatty acids in the ester fraction. In one embodiment, at least about 8% by weight of the fatty acids in the ester fraction is EPA. In some embodiments, the amount of EPA in the ester fraction is at least about 2% by weight of the total omega-3 fatty acids in the ester fraction.
- DHA docosahexaenoic acid
- the present invention is also directed to an oil comprising an ester fraction, wherein at least about 20% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and at least about 20% by weight of the fatty acids in the ester fraction is eicosapentaenoic acid (EPA). In some embodiments, from about 0.1 % to about 5% by weight of the fatty acids in the ester fraction is DPA n-3.
- DHA docosahexaenoic acid
- EPA eicosapentaenoic acid
- the present invention is also directed to an oil comprising an ester fraction, wherein at least about 30% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and at least about 30% by weight of the fatty acids in the ester fraction is eicosapentaenoic acid (EPA). In some embodiments, from about 0.1 % to about 5% by weight of the fatty acids in the ester fraction is DPA n-3.
- DHA docosahexaenoic acid
- EPA eicosapentaenoic acid
- the present invention is also directed to an oil comprising an ester fraction, wherein at least about 65% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and at least about 15% by weight of the fatty acids in the ester fraction is eicosapentaenoic acid (EPA). In some embodiments, from about 0.1 % to about 5% by weight of the fatty acids in the ester fraction is DPA n-3.
- DHA docosahexaenoic acid
- EPA eicosapentaenoic acid
- the present invention is also directed to an oil comprising an ester fraction, wherein at least about 50% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and at least about 25% by weight of the fatty acids in the ester fraction is eicosapentaenoic acid (EPA). In some embodiments, from about 0.1 % to about 5% by weight of the fatty acids in the ester fraction is DP A n-3.
- DHA docosahexaenoic acid
- EPA eicosapentaenoic acid
- the present invention is also directed to a process for separation and concentration of an oil comprising esters of polyunsaturated fatty acids, the process comprising subjecting the oil to at least one distillation step, wherein a first distillation step comprises feeding the oil to at least one apparatus and subjecting the oil to conditions to remove low-boiling compounds in a distillate.
- the oil is a microbial or marine oil.
- the oil is a microbial oil produced from a microorganism.
- the microorganism is selected from the group comprising microalgae, bacteria, fungi and protists.
- the present invention is directed to a food, supplement, or pharmaceutical composition comprising an oil of the invention.
- enriched oil compositions comprising polyunsaturated fatty acids; compositions containing the enriched oil compositions; and methods of making and using the enriched oil compositions.
- Polyunsaturated fatty acids are classified based on the position of the first double bond from the methyl end of the fatty acid; omega-3 (n-3) fatty acids contain a first double bond at the third carbon counting from the methyl end, while omega-6 (n-6) fatty acids contain a first double bond at the sixth carbon.
- DHA docosahexaenoic acid
- LC-PUFA long chain polyunsaturated fatty acid
- the PUFA is selected from an omega-3 fatty acid, an omega-6 fatty acid, and mixtures thereof.
- the PUFA is selected from docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), arachidonic acid (ARA), gamma-linolenic acid (GLA), dihomo-gamma-linolenic acid (DGLA), stearidonic acid (SDA), and mixtures thereof.
- DHA docosahexaenoic acid
- EPA eicosapentaenoic acid
- DPA docosapentaenoic acid
- ARA arachidonic acid
- GLA gamma-linolenic acid
- DGLA dihomo-gamma-linolenic acid
- SDA stearidonic acid
- the PUFA is selected from DHA, DPA, EPA, and mixtures thereof.
- the PUFA is DHA.
- the PUFA is DPA.
- the oil comprises one or more PUFAs.
- the oil comprises at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98%, or at least about 99% PUFA.
- the PUFA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the PUFA is the % by weight of the oil.
- the % by weight of the PUFA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% by weight DHA.
- the DHA is in ester form.
- the ester is an ethyl ester.
- the % by weight of DHA is the % by weight of the oil.
- the % by weight of the DHA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises about 3% to about 13%, about 4% to about 12%, about 5% to about 11%, about 6% to about 10%, or about 7% to about 9% DPA n-3 and DPA n-6.
- the DPA n-3 and DPA n-6 is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DPA n-3 and DPA n-6 is the % by weight of the oil.
- the % by weight of the DPA n-3 and the DPA n-6 is the % by weight of the fatty acids in the ester fraction.
- the oil comprises from about 0.5% to about 5%, about
- the DPA n- 3 is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DPA n-3 is the % by weight of the oil.
- the % by weight of the DPA n-3 is the % by weight of the fatty acids in an ester fraction.
- the oil comprises about 2% to about 8%, about 3% to about 7%, or about 4% to about 6% DPA n-6.
- the DPA n-6 is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DPA n-6 is the % by weight of the oil.
- the % by weight of the DPA n-6 is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the EPA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the EPA is the % by weight of the oil.
- the % by weight of the EPA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises from about 0.1 % to about 5%, about
- the EPA is in ester form. In a more preferred embodiment, the ester is an ethyl ester. In a preferred embodiment, the % by weight of the EPA is the % by weight of the oil. In a more preferred embodiment, the % by weight of the EPA is the % by weight of the fatty acids in an ester fraction. [0029] In some embodiments, the oil comprises less than about 5%, less than about
- the ARA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the ARA is the % by weight of the oil.
- the % by weight of the ARA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the GLA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the GLA is the % by weight of the oil.
- the % by weight of the GLA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the DGLA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DGLA is the % by weight of the oil.
- the % by weight of the DGLA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the SDA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the SDA is the % by weight of the oil.
- the % by weight of the SDA is the % by weight of the fatty acids in an ester fraction.
- the comprises less than about 5%, less than about 4%, less than about 3%, less than about 2.5%, less than about 2%, less than about 2%, less than about 1.5%, less than about 1%, or less than about 0.5% of a polyunsaturated fatty acid having greater than 22 carbons (very long chain PUFAs).
- the very long chain PUFA is 7,10,13,16,19,22,25 octacosaoctaenoic acid (C28:8).
- the oil comprises 0% 7,10,13,16,19,22,25 octacosaoctaenoic acid (C28:8).
- the very long chain PUFA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the very long chain PUFA is the % by weight of the oil.
- the % by weight of the very long chain PUFA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% EPA.
- the EPA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the EPA is the % by weight of the oil.
- the % by weight of the EPA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the DHA is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DHA is the % by weight of the oil.
- the % by weight of the DHA is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- DPA n-3 and DPA n-6 are in ester form.
- the ester is an ethyl ester.
- the % by weight of the DPA n-3 and DPA n-6 is the % by weight of the oil.
- the % by weight of the DPA n-3 and DPA n-6 is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the DPA n-3 is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DPA n-3 is the % by weight of the oil.
- the % by weight of the DPA n-3 is the % by weight of the fatty acids in an ester fraction.
- the oil comprises less than about 5%, less than about
- the DPA n-6 is in ester form.
- the ester is an ethyl ester.
- the % by weight of the DPA n-6 is the % by weight of the oil.
- the % by weight of the DPA n-6 is the % by weight of the fatty acids of the ester fraction.
- the oil comprises an ester fraction wherein at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98%, or at least about 99% by weight of the fatty acids in the ester fraction is docosahexaenoic acid (DHA) and the amount of DHA in the ester fraction is at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90% by weight of the total omega-3 fatty acids in the ester fraction.
- DHA docosahexaenoic acid
- At least about 8%, at least about 10%, at least about 15%, at least about 20%, at least about 35%, at least about 40% by weight of the fatty acids in the ester fraction is EPA.
- the amount of EPA in the ester fraction is at least about 2%, at least about 3%, at least about 4%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25% by weight of the total omega-3 fatty acids in the ester fraction.
- the oil comprises an ester fraction of at least about
- At least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% by weight of the fatty acids in the ester fraction is DHA.
- from about 0.5% to about 5%, about 1% to about 5%, or about 3% to about 4% by weight of the fatty acids in the ester fraction is DPA n-3.
- the DHA content of the fatty acids in the ester fraction is at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% by weight of the amount of DHA and DPA n-3 content of the fatty acids in the ester fraction.
- the DPA n-3 content of the fatty acids in the ester fraction is from about 0.5% to about 5%, about 1% to about 5%, or about 3% to about 4% of the DHA and DPA n-3 content of the fatty acids in the ester fraction.
- the DHA, DPA n-3 and DPA n-6 content of the fatty acids of the ester fraction is at least about 80%, at least about 85%, at least about 90%, at least about 91 %, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% of the total amount of fatty acids in the ester fraction.
- the DHA content of the fatty acids in the ester fraction is at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% of the DHA, DPA n-3 and DPA n- 6 content of the fatty acids in the ester fraction.
- the ester fraction is an ethyl ester.
- the DHA and EPA content of the fatty acids in the ester fraction is at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% of the total amount of fatty acids in the ester fraction.
- the DHA content of the fatty acids in the ester fraction is an amount of at least about 80%, at least about 85%, at least about 90%, at least about 91 %, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% by weight of the total amount of fatty acids in the ester fraction.
- the EPA content of the fatty acids in the ester fraction is less than about 5%, less than about 4%, less than about 3%, less than about 2.5%, less than about 2%, less than about 2%, less than about 1.5%, less than about 1 %, or less than about 0.5% of the total amount of fatty acids in the ester fraction.
- the ester fraction is an ethyl ester.
- the DHA and EPA content of the fatty acids in the ester fraction is at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% of the total amount of fatty acids in the ester fraction.
- the EPA content of the fatty acids in the ester fraction is an amount of at least about 80%, at least about 85%, at least about 90%, at least about 91%, at least about 92%, at least about 93%, at least about 94%, at least about 95%, at least about 96%, at least about 97%, at least about 98% or at least about 99% by weight of the total amount of fatty acids.
- the DHA content of the fatty acids in the ester fraction is less than about 5%, less than about 4%, less than about 3%, less than about 2.5%, less than about 2%, less than about 2%, less than about 1.5%, less than about 1 %, or less than about 0.5% if the total amount of fatty acids in the ester fraction.
- the ester fraction is an ethyl ester.
- the total isomer value of the oil is less than 5%, less than 4.5%, less than 4%, less than 3.5%, less than 3%, less than 2.5%, less than 2%, less than 1.5%, less than 1 %, less than 0.5%, less than 0.1 %, or 0%.
- the EPA isomer value of the oil is less than 5%, less than 4.5%, less than 4%, less than 3.5%, less than 3%, less than 2.5%, less than 2%, less than 1.5%, less than 1 %, less than 0.5%, less than 0.1 %, or 0%.
- the DHA isomer value of the oil is less than 5%, less than 4.5%, less than 4%, less than 3.5%, less than 3%, less than 2.5%, less than 2%, less than 1.5%, less than 1 %, less than 0.5%, less than 0.1 %, or 0%.
- the amount of DHA in the oil per gram of oil is from about 100 mg to about 300 mg, about 100 mg to about 600 mg, about 100 mg to about 800 mg, about 100 mg to about 900 mg, about 100 mg to about 950-mg, about 800 to about 950 mg, or 0 to about 100 mg.
- the amount of EPA in the oil per gram of oil is from about 100 mg to about 300 mg, about 100 mg to about 600 mg, about 100 mg to about 800 mg, about 100 mg to about 900 mg, about 100 mg to about 950-mg, about 800 to about 950 mg, or 0 to about 100 mg.
- the oil is a microbial or marine oil.
- microbial oil Oil produced by a microorganism or obtained from a microbial cell is referred to as "microbial oil”. Oil produced by algae and/or fungi is referred to as an algal and/or a fungal oil, respectively.
- a "microorganism” refers to organisms such as algae, bacteria, fungi, protist, yeast, and combinations thereof, e.g., unicellular organisms.
- a microorganism includes but is not limited to, golden algae (e.g., microorganisms of the kingdom Stramenopiles); green algae; diatoms; dinoflagellates (e.g., microorganisms of the order Dinophyceae including members of the genus Crypthecodinium such as, for example, Crypthecodinium cohnii or C.
- golden algae e.g., microorganisms of the kingdom Stramenopiles
- green algae diatoms
- dinoflagellates e.g., microorganisms of the order Dinophyceae including members of the genus Crypthecodinium such as, for example, Crypthecodinium cohnii or C.
- microalgae of the order Thraustochytriales yeast (Ascomycetes or Basidiomycetes); and fungi of the genera Mucor, Mortierella, including but not limited to Mortierella alpina and Mortierella sect, schmuckeri, and Pythium, including but not limited to Pythium insidiosum.
- the microorganisms are from the genus Mortierella, genus
- the microorganisms are from Crypthecodinium Cohnii.
- the microorganisms are from Mortierella alpina.
- the microorganisms are from Schizochytrium sp.
- the microorganisms are selected from Crypthecodinium Cohnii, Mortierella alpina, Schizochytrium sp. , and mixtures thereof.
- the microorganisms include, but are not limited to, microorganisms belonging to the genus Mortierella, genus Conidiobolus, genus Pythium, genus Phytophthora, genus Penicillium, genus Cladosporium, genus Mucor, genus Fusarium, genus Aspergillus, genus Rhodotorula, genus Entomophthora, genus Echinosporangium, and genus Saprolegnia.
- the microorganisms are from microalgae of the order Thraustochytriales, which includes, but is not limited to, the genera
- Thraustochytrium (species include arudimentale, aureum, benthicola, globosum, kinnei, motivum, multirudimentale, pachydermum, proliferum, roseum, striatum); the genera Schizochytrium (species include aggregatum, limnaceum, mangrovei, minutum, octosporum); the genera Ulkenia (species include amoeboidea, kerguelensis, minuta, profunda, radiate, sailens, sarkariana, schizochytrops, visurgensis, yorkensis); the genera A uran tiacochytrium ; the genera Oblongichytrium; the genera Sicyoidochytium; the genera Parientichytrium; the genera Botryochytrium; and combinations thereof.
- the microorganisms are from the order Thraustochytriales. In yet another embodiment, the microorganisms are from Thraustochytrium. In still a further embodiment, the microorganisms are from Schizochytrium sp.
- the oil can comprise a marine oil. Examples of suitable fish oils include, but are not limited to, Atlantic fish oil, Pacific fish oil, or Mediterranean fish oil, or any mixture or combination thereof.
- a suitable fish oil can be, but is not limited to, pollack oil, bonito oil, pilchard oil, tilapia oil, tuna oil, sea bass oil, halibut oil, spearfish oil, barracuda oil, cod oil, menhaden oil, sardine oil, anchovy oil, capelin oil, herring oil, mackerel oil, salmonid oil, tuna oil, and shark oil, including any mixture or combination thereof.
- Other marine oils suitable for use herein include, but are not limited to, squid oil, cuttle fish oil, octopus oil, krill oil, seal oil, whale oil, and the like, including any mixture or combination thereof.
- a fatty acid as described herein can be a fatty acid ester or ester.
- a fatty acid ester includes an ester of an omega-3 fatty acid, omega-6 fatty acid, and combinations thereof.
- the fatty acid ester is a DHA ester, an EPA ester, or a combination thereof.
- an oil or fraction thereof as described herein is esterified to produce an oil or fraction thereof comprising fatty acid esters.
- esteer refers to the replacement of the hydrogen in the carboxylic acid group of the fatty acid molecule with another substituent.
- esters examples include methyl, ethyl, propyl, butyl, pentyl, t-butyl, benzyl, nitrobenzyl, methoxybenzyl, benzhydryl, and trichloroethyl.
- the ester is a carboxylic acid protective ester group, esters with aralkyl (e.g.
- esters with lower alkenyl e.g., allyl, 2-butenyl
- esters with lower-alkoxy-lower-alkyl e.g., methoxymethyl, 2-methoxyethyl, 2-ethoxy ethyl
- esters with lower-alkanoyloxy-lower-alkyl e.g.
- esters with lower-alkoxycarbonyl-lower-alkyl e.g., methoxycarbonylmethyl, isopropoxycarbonylmethyl
- esters with carboxy-lower alkyl e.g., carboxymethyl
- esters with lower-alkoxycarbonyloxy-lower-alkyl e.g., 1 - (ethoxycarbonyloxy)ethyl, l -(cyclohexyloxycarbonyloxy)ethyl
- esters with carbamoyloxy- lower alkyl e.g., carbamoyloxymethyl
- the added substituent is a linear or cyclic hydrocarbon group, e.g., a C1 -C6 alkyl, C1 -C6 cycloalkyl, C1 -C6 alkenyl, or C1 -C6 aryl ester.
- the ester is an alkyl ester, e.g., a methyl ester, ethyl ester or propyl ester.
- the ester substituent is added to the free fatty acid molecule when the fatty acid is in a purified or semi-purified state.
- Fatty acid esters in particular polyunsaturated fatty acid esters, can be made in ways that are known to one of ordinary skill in the art.
- tri-acyl glycerides, di-acyl glycerides, and /or mono-acyl glycerides that contain fatty acids, particularly poly-unsaturated fatty acids, can be reacted with an alcohol in the presence of an acid or a base to produce esters.
- the disclosure of U. S. Patent Application No. 12/163,555, that published as U. S. Patent Application Pre-Grant Publication No. 2009/0023808, is incorporated by reference herein in its entirety.
- Alcohols can include, for example, Ci-C 6 alkyl alcohols, for example, ethanol, methanol, n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, tert-butanol, n- pentanol, and n-hexanol.
- the alcohol can be used as the reaction solvent and co-reactant, either alone or with a co-solvent.
- the amount of the alcohol can range from 25 % to 50 % by weight of the reaction mixture, including all values and subranges therebetween as if explicitly written out.
- the amount of alcohol in the reaction mixture can be 30%, 35%, 40% or 45% by weight of the reaction mixture.
- the base can be, for example, a metal alkyloxide.
- Metal alkyloxides include sodium ethoxide, sodium methoxide, sodium n-propoxide, sodium iso-propoxide, sodium n- butoxide, sodium iso-butoxide, sodium sec-butoxide, sodium, tert-butoxide, sodium n- pentoxide, sodium n-hexoxide, lithium ethoxide, lithium methoxide, lithium n-propoxide, lithium iso-propoxide, lithium n-butoxide, lithium iso-butoxide, lithium sec-butoxide, lithium, tert-butoxide, lithium n-pentoxide, lithium n-hexoxide, potassium ethoxide, potassium methoxide, potassium n-propoxide, potassium iso-propoxide, potassium n- butoxide, potassium iso-butoxide, potassium sec-butoxide, potassium, tert-butoxide, potassium n-pentoxid
- the base can be made by adding sodium metal, potassium metal, or lithium metal to an alcoholic solution.
- the base can be made by adding a metal hydride, such as lithium hydride, sodium hydride, or potassium hydride, to an alcoholic solution.
- a metal hydride such as lithium hydride, sodium hydride, or potassium hydride
- the ratio of base to oil, on a weight: weight basis can, for example, range from
- the ratio of base to oil, on a weight to weight basis can be 2: 1 , 3: 1, 4: 1 , 5: 1, 6: 1, 7: 1, 8:1 , 9: 1, 10: 1, 20: 1 , 30:1, 40: 1, 50: 1, 60: 1, 70: 1, 80:1, 90: 1, 100: 1, 200: 1 , 300:1 , 400: 1, 500;1, 600: 1, 700: 1, 800: 1 , or 900: 1.
- the esterification reaction can be run at a temperature ranging from 10 °C to
- the esterification reaction can be run at 20 °C, 30 °C, 40 °C, 50 °C, 60 °C, 70 °C, 80 °C, or 90 °C.
- the esterification reaction can be run open to the atmosphere, or under an inert atmosphere such as nitrogen or argon.
- Workup and isolation of the fatty acid esters can be done in ways known to one of ordinary skill, for example, by extraction with an organic solvent and / or water.
- the organic solvent can be, for example, pentane, hexane, di-ethyl ether, ethyl acetate, or a combination of these.
- the water can optionally contain other substances such as sodium bicarbonate, sodium carbonate, ammonium chloride and / or dilute mineral acid.
- the oil is transesterified to convert at least part of the ester fraction in the oil to a triglyceride fraction.
- Transesterification in particular transesterification of polyunsaturated fatty acid esters, can be made in ways that are known to one of ordinary skill in the art.
- any concentrating, reacting, and/or purifying technique can be combined with any other concentrating, reacting, and/or purifying technique to produce microbial oils enriched in: polyunsaturated fatty acids, their esters, their salts, aldehydes thereof and/or alcohols thereof.
- the enrichment techniques can be used in any order and combination.
- the present invention is a food, supplement, or pharmaceutical composition comprising an oil of the invention.
- the pharmaceutical composition can contain a pharmaceutically acceptable carrier.
- the composition is a food product.
- a food product is any food for non-human animal or human consumption, and includes both solid and liquid compositions.
- a food product can be an additive to animal or human foods.
- Foods include, but are not limited to, common foods; liquid products, including milks, beverages, therapeutic drinks, and nutritional drinks; functional foods; supplements; nutraceuticals; infant formulas, including formulas for pre-mature infants; foods for pregnant or nursing women; foods for adults; geriatric foods; and animal foods.
- the composition is an animal feed.
- An "animal” includes non-human organisms belonging to the kingdom Animalia, and includes, without limitation, aquatic animals and terrestrial animals.
- the term "animal feed” or "animal food” refers to any food intended for non-human animals, whether for fish; commercial fish; ornamental fish; fish larvae; bivalves; mollusks; crustaceans; shellfish; shrimp; larval shrimp; artemia; rotifers; brine shrimp; filter feeders; amphibians; reptiles; mammals; domestic animals; farm animals; zoo animals; sport animals; breeding stock; racing animals; show animals; heirloom animals; rare or endangered animals; companion animals; pet animals such as dogs, cats, guinea pigs, rabbits, rats, mice, or horses; primates such as monkeys (e.g., cebus, rhesus, African green, patas, cynomolgus, and cercopithecus), apes, orangutans, bab
- the composition is a feed or feed supplement for any animal whose meat or products are consumed by humans, such as any animal from which meat, eggs, or milk is derived for human consumption.
- nutrients such as LC-PUFAs can be incorporated into the flesh, milk, eggs or other products of such animals to increase their content of these nutrients.
- the present invention is also directed to a process for separation and concentration of an oil comprising esters of polyunsaturated fatty acids to produce an oil.
- the process comprises subjecting the oil to at least one distillation step, wherein a first distillation step comprises feeding the oil to at least one apparatus and subjecting the oil to conditions to remove low-boiling compounds in a distillate.
- a first distillation step comprises feeding the oil to at least one apparatus and subjecting the oil to conditions to remove low-boiling compounds in a distillate.
- at least a portion of eicosapentaenoic acid (EPA) is removed in the distillate.
- at least about 5%, at least about 10%, at least about 15%, at least about 20% of EPA is in the distillate of the first distillation step.
- LC-PUFA long-chain polyunsaturated fatty acid
- one LC-PUFA is EPA.
- the second LC-PUFA is DHA.
- one LC-PUFA is EPA and the second LC-PUFA is DHA.
- LC-PUFA long-chain polyunsaturated fatty acid
- one LC-PUFA is EPA.
- the second LC-PUFA is DHA.
- one LC-PUFA is EPA and the second LC-PUFA is DHA.
- the process comprises short path distillation, fractional distillation, falling-film evaporator, wiped-film evaporator, or combinations thereof. In a preferred embodiment, the process comprises fractional distillation. [0083] In some embodiments, the apparatus is a fractionating column.
- the column comprises a rectification section.
- the column has at least about 1 meter, at least about 2 meter, or at least about 3 meter of structured packing, having at least about 3-4, at least about 4-5, at least about 5-6, at least about 6-7, at least about 7-8, at least about 8-9, at least about 9-10, at least about 10-11 , at least about 1 1 -12, or at least about 12-13 theoretical stages.
- the column is attached to a vacuum.
- the pressure at the top of the column is less than about 4 mbar, less than about 3.5 mbar, less than about 3 mbar, less than about 2.5 mbar, less than about 2 mbar, or less than about 1.5 mbar.
- the pressure drop of the column is less than about 10 mbar, less than about 9 mbar, less than about 8 mbar, less than about 7 mbar, less than about 6 mbar, less than about 5 mbar, less than about 4 mbar, or less than about 3 mbar.
- the apparatus is a fractionating column or short-path distillation.
- the fractionating column is attached to a wiped-film evaporator.
- the apparatus of each distillation step may be the same apparatus or may be in series.
- feeding the oil to at least one apparatus comprises a mid-column feed. In some embodiments, feeding the oil to at least one apparatus comprises an evaporator feed.
- the oil subjected to a first distillation step is separated at the residue end and the distillate end in an amount of at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, or at least about 80% by weight.
- the oil collected at the residue end comprises at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 85%, or at least about 90% by weight EPA and DHA.
- the oil collected at the distillate end comprises at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 85%, or at least about 90% by weight polyunsaturated fatty acids having less than 20 carbons.
- the oil subjected to the second distillation step is separated at the residue end and the distillate end in an amount of at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, or at least about 80% by weight.
- the oil collected at the residue end comprises at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 85%, or at least about 90% by weight EPA.
- the oil collected at the distillate end comprises at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 85%, or at least about 90% by weight DHA.
- the oil subjected to the third distillation step is separated at the residue end and the distillate end in an amount of at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, or at least about 80% by weight.
- the oil collected at the residue end comprises at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 85%, or at least about 90% by weight EPA.
- the oil collected at the distillate end comprises at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 85%, or at least about 90% by weight DHA.
- the at least one distillation step comprises heating wherein the temperature is less than about 275 °C, less than about 250 °C, less than about 225 °C, less than about 200 °C, less than about 190 °C, less than about 180 °C, or less than about 170 °C, from about 100 0 C to about 250 °C, from about 125 0 C to 225 °C, from about 150 0 C to 200 °C, or from about 160 0 C to 190 °C.
- the reflux ratio is less than about 5, less than about 4.5, less than about 4, less than about 3.5, less than about 3, less than about 2.5, less than about 2, less than about 1.5, less than about 1, or less than about 0.5.
- the present invention is also directed to an oil produced by any of the processes disclosed herein.
- a crude oil was produced through fermentation of Schizochytrium sp.
- Table 1 shows the fatty acid profile of the starting oil.
- the top oil layer was then transferred to a clean 1L round- bottomed flask and a solution of sodium ethoxide (0.32 g) in ethanol (12.0 g) was added.
- the mixture was again heated to 75°C while stirring under a N2 atmosphere and then maintained at this temperature for 1 hour.
- the ethanol was removed using a rotary evaporator, the residue was washed with a citric acid solution (1 % w/w) until the pH of the aqueous washing portions was no longer basic, washed with water, and dried under vacuum.
- the residue from the first pass was fed through the short path distillation apparatus, resulting in 131 mg/g EPA and 373 mg/g DHA in the distillate (Sample 2D) and 84 mg/g EPA and 717 mg/g DHA in the residue (Sample 2R).
- the residue from the second pass was fed through the short path distillation apparatus, resulting in 86 mg/g EPA and 742 mg/g DHA in the distillate (Sample 3D). The residue could not be sampled due to the viscosity (Sample 3R).
- the residue from the first pass was fed through the short path distillation apparatus, resulting in 76 mg/g EPA and 766 mg/g DHA in the distillate (Sample 2D). The residue could not be sampled due to the viscosity (Sample 2R).
- the distillate from the second pass was fed through the short path distillation apparatus, resulting in 96 mg/g EPA and 786 mg/g DHA in the distillate (Sample 3D) and 22 mg/g EPA and 805 mg/g DHA residue in the residue (Sample 3R). Results are shown in Table 5.
- a crude oil was produced through fermentation of Schizochytrium sp.
- the mixture was again heated to 75°C while stirring under a N2 atmosphere and then maintained at this temperature for 1 hour.
- the ethanol was removed using a rotary evaporator, washed with a citric acid solution (1 % w/w) until the pH of the aqueous washing portions was no longer basic, washed with water, and dried under vacuum.
- a crude fish oil was subjected to a separation and concentration process.
- Transesterification An esterification reaction between the purified marine oil and ethyl alcohol, using sodium ethoxide as a catalyst, was used to produce a marine oil ethyl ester. Ethanol and sodium ethoxide was added to a purified marine oil that had been heated. The glycerol was separated from the marine oil. Ethanol and sodium ethoxide was then added again to the marine oil (after removal of the glycerol). The ethyl ester marine oil formed was centrifuged for further glycerol removal. The sodium ethoxide was neutralized by 5% addition by weight of the marine oil of a 9% citric acid solution. The acid wash layer was separated from the ethyl ester marine oil, water was added, and the ethyl ester marine oil was dried.
- a crude fish oil was subjected to a separation and concentration process.
- a falling-film evaporator with a rectification column followed by short path distillation (SPD) was evaluated.
- the column contained approximately 1 meter of packing having approximately 3-4 theoretical stages.
- An ethyl ester marine oil was fed through the recycle stream at a temperature of 205°C. Concentration results are shown in Table 7. Isomer results are shown in Table 8.
- a crude fish oil was subjected to a separation and concentration process. 2 columns in series (each a falling-film evaporator with a rectification column) followed by short path distillation was evaluated.
- the column-residue sample in Example 4 was fed through a second falling-film evaporator with a rectification column having approximately 2 meter of packing and a mid-column liquid distributor under the same conditions as in Example 4. Concentration results are shown in Table 11. Isomer results are shown in Table 12.
- a crude fish oil was subjected to a separation and concentration process.
- a fractional distillation column with an external condenser followed by short path distillation (SPD) was evaluated.
- the external condenser was a wiped-film evaporator.
- the column was packed with 3 meters of packing, having approximately 8-9 theoretical stages of separation with a mid-column feed. Concentration results are shown in Table 13. Isomer results are shown in Table 14.
- a crude fish oil was subjected to a separation and concentration process.
- a fractional distillation column with an external condenser followed by short path distillation (SPD) was evaluated.
- the external condenser was a wiped-film evaporator.
- the column was packed with 3 meters of packing, having approximately 8-9 theoretical stages of separation with an evaporator feed. Concentration results are shown in Table 15. Isomer results are shown in Table 16.
- a crude fish oil was subjected to a separation and concentration process.
- a fractional distillation column with an external condenser followed by a second fractional distillation column with an external condenser followed by a short path distillation (SPD) was evaluated.
- the external condenser was a wiped-film evaporator. Both columns were packed with 2 meters of packing, having approximately 8-9 theoretical stages of separation with mid- column feed. Concentration results are shown in Table 17. Isomer results are shown in Table 18.
- Table 17 Column followed by Second Column, followed by Short-Path Distillation, 2m packing, EPA/DHA concentration
- DHA was subjected to a separation and concentration process.
- a fractional distillation column with an external condenser followed by a second fractional distillation column with an external condenser followed by a short path distillation (SPD) was evaluated.
- the external condenser was a wiped-film evaporator.
- the residue was passed through a second column and the EPA and DHA concentrations in the distillate and residue were measured (Table 23).
- the residue from the second column was passed through a short path distillation column and the EPA and DHA concentrations in the distillate and residue were measured (Table 24).
- the EPA and DHA concentrations of each sample were measured at different time intervals during the processing.
- a crude oil was produced through fermentation of Schizochytrium sp. The oil was subjected to a transesterification step to produce ethyl esters of polyunsaturated fatty acids.
- a crude oil was produced through fermentation of Schizochytrium sp. The oil was subjected to a transesterification step to produce ethyl esters of polyunsaturated fatty acids.
- the oil was fractionated via a first pass through a fractional distillation column.
- the distillate contained 222 mg/g EPA and 218 mg/g DHA (sample ID).
- the residue contained 175 mg/g EPA and 611 mg/g DHA (sample 1R).
- the distillate from this first pass was fractionated via a second pass through a fractional distillation column.
- the distillate from this was 77 mg/g EPA and 34 mg/g DHA (sample 3D) and the residue from this was 291 mg/g EPA and 331 mg/g DHA (sample 3R).
- the residue from the first pass was fractionated via a second pass through a fractional distillation column.
- the distillate from this was 181 mg/g EPA and 624 mg/g DHA (sample 2D) and the residue from this could not be sampled due to viscosity.
- Sample 2D was passed through a short path distillation apparatus.
- the distillate from this was 256 mg/g EPA and 559 mg/g DHA (sample 4D) and the residue was 105 mg/g EPA and 697 mg/g DHA (sample 4R). All passes through the fractionation column and/or short path distillation apparatus used a temperature range from 110°C to 180°C and vacuum of approximately 20-25mtorr. Results are shown in Table 28.
- a crude oil was produced through fermentation of Cryptochodinium cohnii.
- the oil was subjected to a transesterifi cation step to produce ethyl esters of polyunsaturated fatty acids.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Pediatric Medicine (AREA)
- Birds (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Fats And Perfumes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Dairy Products (AREA)
- Edible Oils And Fats (AREA)
- Cosmetics (AREA)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201680071077.5A CN108289470A (zh) | 2015-10-05 | 2016-10-05 | 油组合物和制备方法 |
BR112018006807-1A BR112018006807B1 (pt) | 2015-10-05 | 2016-10-05 | Processo para a separação e concentração de um óleo compreendendo ésteres de ácidos graxos poli-insaturados |
JP2018516573A JP6947370B2 (ja) | 2015-10-05 | 2016-10-05 | 油組成物および製造方法 |
CA3001018A CA3001018A1 (en) | 2015-10-05 | 2016-10-05 | Oil compositions and methods of making |
MX2018004128A MX2018004128A (es) | 2015-10-05 | 2016-10-05 | Composiciones de aceite y metodos para elaborarlas. |
EP16854262.9A EP3358960A4 (en) | 2015-10-05 | 2016-10-05 | OIL COMPOSITIONS AND METHOD OF PREPARING THEREOF |
US15/762,244 US20190071618A1 (en) | 2015-10-05 | 2016-10-05 | Oil compositions and methods of making |
NZ741784A NZ741784B2 (en) | 2016-10-05 | Oil compositions and methods of making | |
AU2016336354A AU2016336354B2 (en) | 2015-10-05 | 2016-10-05 | Oil compositions and methods of making |
KR1020187012252A KR20180063217A (ko) | 2015-10-05 | 2016-10-05 | 오일 조성물 및 제조 방법 |
IL258381A IL258381A (en) | 2015-10-05 | 2018-03-26 | Petroleum preparations and methods for their preparation |
HK19100923.1A HK1258568A1 (zh) | 2015-10-05 | 2019-01-18 | 油組合物和製備方法 |
AU2021205085A AU2021205085B2 (en) | 2015-10-05 | 2021-07-15 | Oil compositions and methods of making |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562237320P | 2015-10-05 | 2015-10-05 | |
US62/237,320 | 2015-10-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2017062523A2 true WO2017062523A2 (en) | 2017-04-13 |
WO2017062523A3 WO2017062523A3 (en) | 2017-05-18 |
Family
ID=58488476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2016/055599 WO2017062523A2 (en) | 2015-10-05 | 2016-10-05 | Oil compositions and methods of making |
Country Status (13)
Country | Link |
---|---|
US (1) | US20190071618A1 (ja) |
EP (1) | EP3358960A4 (ja) |
JP (1) | JP6947370B2 (ja) |
KR (1) | KR20180063217A (ja) |
CN (1) | CN108289470A (ja) |
AU (2) | AU2016336354B2 (ja) |
BR (1) | BR112018006807B1 (ja) |
CA (1) | CA3001018A1 (ja) |
HK (1) | HK1258568A1 (ja) |
IL (1) | IL258381A (ja) |
MX (1) | MX2018004128A (ja) |
SG (1) | SG10202003063WA (ja) |
WO (1) | WO2017062523A2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021191385A1 (fr) * | 2020-03-27 | 2021-09-30 | Polaris | Procede de fractionnement d'acides gras a deux carbones de difference par distillation moleculaire |
DE102018010277B4 (de) | 2018-03-29 | 2022-01-13 | Hegla Boraident Gmbh & Co. Kg | Entschichtungsverfahren und Verwendung einer Entschichtungseinrichtung zum Entschichten von Glastafeln, vorzugsweise Verbundglastafeln |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU102019B1 (de) * | 2020-08-26 | 2022-02-28 | K D Pharma Bexbach Gmbh | Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis |
CN115350493A (zh) * | 2022-09-15 | 2022-11-18 | 江苏海莱康生物科技有限公司 | 一种分离提纯鱼油中的二十碳五烯酸乙酯的方法及精馏装置 |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2380809A (en) | 1939-12-11 | 1945-07-31 | Verkinderen Honore | Color couplers for photographic color development |
US5130061A (en) | 1987-05-28 | 1992-07-14 | Innova Di Ridolfi Flora & C. S.A.S. | Process for the extraction of polyunsaturated fatty acid esters from fish oils |
US5215630A (en) | 1991-06-04 | 1993-06-01 | Nippon Suisan Kaisha, Ltd. | Method of purifying eicosapentaenoic acid or the ester derivative thereof by fractional distillation |
JPH05222392A (ja) | 1991-10-28 | 1993-08-31 | Nippon Suisan Kaisha Ltd | 高純度エイコサペンタエン酸またはそのエステルの製造方法 |
JPH09302380A (ja) | 1996-05-10 | 1997-11-25 | Nippon Wax Polymer Kaihatsu Kenkyusho:Kk | エイコサペンタエン酸又はそのエステルの精製方法 |
WO2001051598A1 (en) | 2000-01-11 | 2001-07-19 | Monsanto Technology Llc | Process for making an enriched mixture of polyunsaturated fatty acid esters |
US20080175975A1 (en) | 2005-01-26 | 2008-07-24 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Method For Producing a Dha-Containing Fatty Acid Composition |
WO2009006317A1 (en) | 2007-06-29 | 2009-01-08 | Martek Biosciences Corporation | Production and purification of esters of polyunsaturated fatty acids |
US8057819B2 (en) | 2009-04-28 | 2011-11-15 | Avema Pharma Solutions, Division of PL Development | Stability additives for dry DHA dosage forms |
WO2014152283A1 (en) | 2013-03-15 | 2014-09-25 | Heliae Development, Llc | Direct transesterification of algal biomass for synthesis of fatty acid ethyl esters (faee) |
EP3196280A1 (en) | 2014-09-17 | 2017-07-26 | Nippon Suisan Kaisha, Ltd. | Composition containing eicosapentaenoic acid alkyl ester, and method for producing same |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4792418A (en) * | 1985-08-14 | 1988-12-20 | Century Laboratories, Inc. | Method of extraction and purification of polyunsaturated fatty acids from natural sources |
JP3614177B2 (ja) * | 1992-07-21 | 2005-01-26 | 日本水産株式会社 | 高純度ドコサヘキサエン酸またはそのエステルの 製造方法 |
JPH11246888A (ja) * | 1998-12-14 | 1999-09-14 | Nippon Suisan Kaisha Ltd | 高純度エイコサペンタエン酸またはそのエステルの製造方法 |
US20030060509A1 (en) * | 2001-08-24 | 2003-03-27 | Elswyk Mary Van | Products containing highly unsaturated fatty acids for use by women and their children during stages of preconception, pregnancy and lactation/post-partum |
NO319194B1 (no) * | 2002-11-14 | 2005-06-27 | Pronova Biocare As | Lipase-katalysert forestringsfremgangsmate av marine oljer |
CA2605832C (en) * | 2005-06-16 | 2018-05-08 | Ocean Nutrition Canada Ltd. | Immobilized enzymes and methods of using thereof |
CN101478889A (zh) * | 2006-06-23 | 2009-07-08 | 宝洁公司 | 浓缩型ω-3脂肪酸以及包含它们的混合物 |
MY152880A (en) * | 2006-08-29 | 2014-11-28 | Dsm Ip Assets Bv | Use of dpa(n-6) oils in infant formula |
ITMI20070157A1 (it) * | 2007-01-31 | 2008-08-01 | Adorkem Technology Spa | Processo di arricchimento enzimatico di una miscela contenente omega 3 |
CN102099451B (zh) * | 2008-05-15 | 2015-07-15 | 普罗诺瓦生物医药挪威公司 | 磷虾油提取方法 |
EP2519332B1 (en) * | 2009-12-30 | 2014-03-05 | BASF Pharma (Callanish) Limited | Simulated moving bed chromatographic separation process for the purification of polyunsaturated fatty acids |
JP2014511406A (ja) * | 2011-02-11 | 2014-05-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | エイコサペンタエン酸濃縮物 |
WO2012119745A1 (de) * | 2011-03-08 | 2012-09-13 | Cognis Ip Management Gmbh | Ein verfahren zur destillation von fettsäureestern |
WO2013013210A1 (en) * | 2011-07-21 | 2013-01-24 | Dsm Ip Assets B.V. | Microbial oils enriched in polyunsaturated fatty acids |
WO2013043641A1 (en) * | 2011-09-21 | 2013-03-28 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Method for enrichment of eicosapentaenoic acid and docosahexaenoic acid in source oils |
CN103509651B (zh) * | 2012-06-27 | 2015-01-07 | 浙江海洋学院 | 一种从鱼油精炼副产物中提取富集乙酯型鱼油的方法 |
CN102994236B (zh) * | 2012-12-11 | 2015-03-25 | 成都圆大生物科技有限公司 | 一种制备Omega-3大于90%的脂肪酸乙酯的方法 |
CN103242969B (zh) * | 2013-05-24 | 2014-11-19 | 四川欣美加生物医药有限公司 | 甘油三酯型鱼油制备方法及制备的甘油三酯型鱼油 |
CN103864614B (zh) * | 2014-03-20 | 2015-11-25 | 江苏中邦制药有限公司 | 从微生物发酵的dha油脂中分离纯化dha乙酯的方法 |
CN103951556B (zh) * | 2014-05-09 | 2015-09-09 | 福州大学 | 一种从深海鱼油中分离epa、dpa和dha的蒸馏工艺 |
-
2016
- 2016-10-05 WO PCT/US2016/055599 patent/WO2017062523A2/en active Application Filing
- 2016-10-05 AU AU2016336354A patent/AU2016336354B2/en active Active
- 2016-10-05 MX MX2018004128A patent/MX2018004128A/es unknown
- 2016-10-05 SG SG10202003063WA patent/SG10202003063WA/en unknown
- 2016-10-05 JP JP2018516573A patent/JP6947370B2/ja active Active
- 2016-10-05 EP EP16854262.9A patent/EP3358960A4/en active Pending
- 2016-10-05 BR BR112018006807-1A patent/BR112018006807B1/pt active IP Right Grant
- 2016-10-05 CA CA3001018A patent/CA3001018A1/en active Pending
- 2016-10-05 CN CN201680071077.5A patent/CN108289470A/zh active Pending
- 2016-10-05 KR KR1020187012252A patent/KR20180063217A/ko not_active Application Discontinuation
- 2016-10-05 US US15/762,244 patent/US20190071618A1/en not_active Abandoned
-
2018
- 2018-03-26 IL IL258381A patent/IL258381A/en unknown
-
2019
- 2019-01-18 HK HK19100923.1A patent/HK1258568A1/zh unknown
-
2021
- 2021-07-15 AU AU2021205085A patent/AU2021205085B2/en active Active
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2380809A (en) | 1939-12-11 | 1945-07-31 | Verkinderen Honore | Color couplers for photographic color development |
US5130061A (en) | 1987-05-28 | 1992-07-14 | Innova Di Ridolfi Flora & C. S.A.S. | Process for the extraction of polyunsaturated fatty acid esters from fish oils |
US5215630A (en) | 1991-06-04 | 1993-06-01 | Nippon Suisan Kaisha, Ltd. | Method of purifying eicosapentaenoic acid or the ester derivative thereof by fractional distillation |
JPH05222392A (ja) | 1991-10-28 | 1993-08-31 | Nippon Suisan Kaisha Ltd | 高純度エイコサペンタエン酸またはそのエステルの製造方法 |
JPH09302380A (ja) | 1996-05-10 | 1997-11-25 | Nippon Wax Polymer Kaihatsu Kenkyusho:Kk | エイコサペンタエン酸又はそのエステルの精製方法 |
WO2001051598A1 (en) | 2000-01-11 | 2001-07-19 | Monsanto Technology Llc | Process for making an enriched mixture of polyunsaturated fatty acid esters |
US20080175975A1 (en) | 2005-01-26 | 2008-07-24 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Method For Producing a Dha-Containing Fatty Acid Composition |
WO2009006317A1 (en) | 2007-06-29 | 2009-01-08 | Martek Biosciences Corporation | Production and purification of esters of polyunsaturated fatty acids |
US20140128465A1 (en) | 2007-06-29 | 2014-05-08 | Dsm Ip Assets B.V. | Production and purification of esters of polyunsaturated fatty acids |
US8057819B2 (en) | 2009-04-28 | 2011-11-15 | Avema Pharma Solutions, Division of PL Development | Stability additives for dry DHA dosage forms |
WO2014152283A1 (en) | 2013-03-15 | 2014-09-25 | Heliae Development, Llc | Direct transesterification of algal biomass for synthesis of fatty acid ethyl esters (faee) |
EP3196280A1 (en) | 2014-09-17 | 2017-07-26 | Nippon Suisan Kaisha, Ltd. | Composition containing eicosapentaenoic acid alkyl ester, and method for producing same |
Non-Patent Citations (6)
Title |
---|
ANONYMOUS: "Thin Film Evaporator", BUSS-SMS-CANZLER, 2015, XP055797904, Retrieved from the Internet <URL:https://www.sms-vt.com/technologies/evaporation-technology/thin-film-evaporator/> |
ANONYMOUS: "Wiped film evaporators / thin film evaporators", VTA, 22 May 2019 (2019-05-22), pages 1 - 4, XP055797903, Retrieved from the Internet <URL:https://www.vta-process.de/en/products/evaporators/wiped-film-evaporators.html> |
BERGE, J.P.BARNATHAN, G., ADV. BIOCHEM. ENG. BIOTECHNOL., vol. 96, 2005, pages 49 - 125 |
CATERINA SCIOTTO, SVEIN A. MJOS: "Trans isomers of EPA and DHA in omega-3 products on the European market.", LIPIDS, vol. 47, 1 January 2012 (2012-01-01), pages 659 - 667, XP055656701, DOI: 10.1007/s11745-012-3672-3 |
MJØS SVEIN A., SOLVANG MARIANNE: "Geometrical isomerisation of eicosapentaenoic and docosahexaenoic acid at high temperatures", EUROPEAN JOURNAL OF LIPID SCIENCE TECHNOLOGY, vol. 108, no. 7, 1 July 2006 (2006-07-01), DE , pages 589 - 597, XP055890059, ISSN: 1438-7697, DOI: 10.1002/ejlt.200600055 |
ROCHE, H. M., PROC. NUTR. SOC., vol. 58, 1999, pages 397 - 401 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102018010277B4 (de) | 2018-03-29 | 2022-01-13 | Hegla Boraident Gmbh & Co. Kg | Entschichtungsverfahren und Verwendung einer Entschichtungseinrichtung zum Entschichten von Glastafeln, vorzugsweise Verbundglastafeln |
WO2021191385A1 (fr) * | 2020-03-27 | 2021-09-30 | Polaris | Procede de fractionnement d'acides gras a deux carbones de difference par distillation moleculaire |
FR3108622A1 (fr) * | 2020-03-27 | 2021-10-01 | Polaris | Procédé de fractionnement d’acides gras à deux carbones de différence par distillation moléculaire |
Also Published As
Publication number | Publication date |
---|---|
JP6947370B2 (ja) | 2021-10-13 |
BR112018006807A2 (pt) | 2018-10-16 |
CN108289470A (zh) | 2018-07-17 |
NZ741784A (en) | 2023-09-29 |
US20190071618A1 (en) | 2019-03-07 |
EP3358960A4 (en) | 2019-07-03 |
IL258381A (en) | 2018-05-31 |
WO2017062523A3 (en) | 2017-05-18 |
CA3001018A1 (en) | 2017-04-13 |
MX2018004128A (es) | 2018-05-17 |
EP3358960A2 (en) | 2018-08-15 |
AU2016336354A1 (en) | 2018-05-10 |
AU2016336354B2 (en) | 2021-04-15 |
AU2021205085A1 (en) | 2021-08-12 |
AU2021205085B2 (en) | 2024-01-25 |
JP2018532015A (ja) | 2018-11-01 |
HK1258568A1 (zh) | 2019-11-15 |
KR20180063217A (ko) | 2018-06-11 |
SG10202003063WA (en) | 2020-05-28 |
BR112018006807B1 (pt) | 2023-02-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2021205085B2 (en) | Oil compositions and methods of making | |
EP2734626B1 (en) | Microbial oils enriched in polyunsaturated fatty acids | |
CA2692355C (en) | Production and purification of esters of polyunsaturated fatty acids | |
RU2747879C2 (ru) | Композиции из рафинированного масла и способы их изготовления | |
JP2010519311A (ja) | 長鎖多価不飽和脂肪酸由来のオキシリピンならびにその作製およびその使用方法 | |
JP7242769B2 (ja) | 遊離多価不飽和脂肪酸含有組成物及びその製造方法 | |
US20200369982A1 (en) | Process for production of concentrated polyunsaturated fatty acid oils | |
JP7381491B2 (ja) | 高度不飽和脂肪酸またはそのアルキルエステルを含有する組成物およびその製造方法 | |
US20240117390A1 (en) | Microbial Oil/Lipid and Method for Producing Microbial Oil/Lipid | |
NZ741784B2 (en) | Oil compositions and methods of making | |
WO2012112902A1 (en) | Methods of preparing free polyunsaturated fatty acids | |
WO2019185910A2 (en) | Novel use of substituted 2h-chromens and their derivatives | |
WO2019185941A1 (en) | Novel use of substituted chroman-6-ols with extended lipophilic side chains | |
JP2024004585A (ja) | ω-3高度不飽和脂肪酸含有組成物の製造方法 | |
WO2019185891A1 (en) | Novel use of substituted chroman-6-ols |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16854262 Country of ref document: EP Kind code of ref document: A2 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 258381 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2018516573 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11201802735S Country of ref document: SG |
|
ENP | Entry into the national phase |
Ref document number: 3001018 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 122022022633 Country of ref document: BR Ref document number: MX/A/2018/004128 Country of ref document: MX |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112018006807 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 20187012252 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2016854262 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2016336354 Country of ref document: AU Date of ref document: 20161005 Kind code of ref document: A |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16854262 Country of ref document: EP Kind code of ref document: A2 |
|
ENP | Entry into the national phase |
Ref document number: 112018006807 Country of ref document: BR Kind code of ref document: A2 Effective date: 20180404 |